TWI277615B - Substituted oxazolidinones and their use - Google Patents

Info

Publication number

TWI277615B

TWI277615B TW083120747A TW93120747A TWI277615B TW I277615 B TWI277615 B TW I277615B TW 083120747 A TW083120747 A TW 083120747A TW 93120747 A TW93120747 A TW 93120747A TW I277615 B TWI277615 B TW I277615B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

phenyl

compound

hplc

Prior art date

1999-12-24

Links

• Espacenet
• Global Dossier
• Discuss

• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title abstract description 9
• 238000000034 method Methods 0.000 claims abstract description 189
• 150000001875 compounds Chemical class 0.000 claims abstract description 118
• 238000002360 preparation method Methods 0.000 claims abstract description 33
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
• -1 ketone ketone Chemical class 0.000 claims description 108
• 239000000203 mixture Substances 0.000 claims description 105
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 95
• 239000001257 hydrogen Substances 0.000 claims description 63
• 229910052739 hydrogen Inorganic materials 0.000 claims description 63
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 51
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 39
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• 150000001412 amines Chemical class 0.000 claims description 34
• 230000000875 corresponding effect Effects 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 239000000460 chlorine Substances 0.000 claims description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 21
• 239000008280 blood Substances 0.000 claims description 21
• 210000004369 blood Anatomy 0.000 claims description 21
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
• 208000007536 Thrombosis Diseases 0.000 claims description 18
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
• 125000000468 ketone group Chemical group 0.000 claims description 17
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 16
• 229930192474 thiophene Natural products 0.000 claims description 16
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 229930194542 Keto Natural products 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 229920006395 saturated elastomer Polymers 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 13
• 150000002431 hydrogen Chemical class 0.000 claims description 13
• 150000002923 oximes Chemical class 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 150000001204 N-oxides Chemical class 0.000 claims description 11
• 125000003277 amino group Chemical group 0.000 claims description 11
• XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 11
• 229940079593 drug Drugs 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 230000002265 prevention Effects 0.000 claims description 11
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
• 108010074860 Factor Xa Proteins 0.000 claims description 8
• 230000005764 inhibitory process Effects 0.000 claims description 8
• 150000002576 ketones Chemical class 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 230000002079 cooperative effect Effects 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• 229910052786 argon Inorganic materials 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 239000000463 material Substances 0.000 claims description 6
• 125000000962 organic group Chemical group 0.000 claims description 6
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 239000012535 impurity Substances 0.000 claims description 5
• 238000000338 in vitro Methods 0.000 claims description 5
• 239000012442 inert solvent Substances 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 208000031104 Arterial Occlusive disease Diseases 0.000 claims description 4
• 206010010904 Convulsion Diseases 0.000 claims description 4
• 206010047249 Venous thrombosis Diseases 0.000 claims description 4
• 208000021328 arterial occlusion Diseases 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 238000007796 conventional method Methods 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• 208000010125 myocardial infarction Diseases 0.000 claims description 4
• 239000007800 oxidant agent Substances 0.000 claims description 4
• 230000002093 peripheral effect Effects 0.000 claims description 4
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
• 208000004998 Abdominal Pain Diseases 0.000 claims description 3
• 208000002881 Colic Diseases 0.000 claims description 3
• 208000010378 Pulmonary Embolism Diseases 0.000 claims description 3
• 206010038743 Restlessness Diseases 0.000 claims description 3
• 230000003213 activating effect Effects 0.000 claims description 3
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
• 239000012472 biological sample Substances 0.000 claims description 3
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
• 239000003153 chemical reaction reagent Substances 0.000 claims description 3
• 239000007822 coupling agent Substances 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 201000001320 Atherosclerosis Diseases 0.000 claims description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
• 206010051055 Deep vein thrombosis Diseases 0.000 claims description 2
• 206010028980 Neoplasm Diseases 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 201000011510 cancer Diseases 0.000 claims description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 208000009190 disseminated intravascular coagulation Diseases 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
• 238000007639 printing Methods 0.000 claims description 2
• 238000001356 surgical procedure Methods 0.000 claims description 2
• 230000002792 vascular Effects 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
• 125000006242 amine protecting group Chemical group 0.000 claims 2
• CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 claims 1
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
• 108010014173 Factor X Proteins 0.000 claims 1
• 208000001613 Gambling Diseases 0.000 claims 1
• 229910002651 NO3 Inorganic materials 0.000 claims 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
• 208000002193 Pain Diseases 0.000 claims 1
• 239000002671 adjuvant Substances 0.000 claims 1
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
• 206010003246 arthritis Diseases 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 230000002490 cerebral effect Effects 0.000 claims 1
• 230000001112 coagulating effect Effects 0.000 claims 1
• 150000002118 epoxides Chemical class 0.000 claims 1
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
• 239000012948 isocyanate Substances 0.000 claims 1
• 150000002513 isocyanates Chemical class 0.000 claims 1
• 238000010899 nucleation Methods 0.000 claims 1
• 230000001590 oxidative effect Effects 0.000 claims 1
• 238000007493 shaping process Methods 0.000 claims 1
• 239000004575 stone Substances 0.000 claims 1
• 230000023555 blood coagulation Effects 0.000 abstract description 7
• 208000035475 disorder Diseases 0.000 abstract description 5
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• 238000011321 prophylaxis Methods 0.000 abstract 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 151
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 104
• 239000002585 base Substances 0.000 description 85
• 239000007789 gas Substances 0.000 description 72
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
• 239000000243 solution Substances 0.000 description 42
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• 235000019439 ethyl acetate Nutrition 0.000 description 37
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 36
• 239000000047 product Substances 0.000 description 35
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
• 239000000126 substance Substances 0.000 description 27
• 239000002023 wood Substances 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 24
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
• 230000002829 reductive effect Effects 0.000 description 22
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 14
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• 125000000753 cycloalkyl group Chemical group 0.000 description 12
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 239000011541 reaction mixture Substances 0.000 description 12
• 239000011734 sodium Substances 0.000 description 12
• 238000005160 1H NMR spectroscopy Methods 0.000 description 11
• 230000014759 maintenance of location Effects 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
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• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
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• 230000015271 coagulation Effects 0.000 description 8
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• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 8
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 7
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• 125000004432 carbon atom Chemical group C* 0.000 description 7
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